Be patient with your boyfriend. Building confidence doesn't happen overnight, because lacking self-esteem takes a lifetime to learn. It will take time for your boyfriend to change ingrained patterns of behavior that are associated with lack of confidence. These behaviors include, but are not limited to, social isolation, problems receiving criticism and being defensive. Avoid being punitive or critical, by not repeatedly pointing out multiple problems with something he has said or done. Reduce your tendency to react immediately when your boyfriend does something you ordinarily jump on and use as an example of "this is what you always do."

Maintain your own sense of confidence. Monitor your behavior when you spend time with your boyfriend. Patterns of behavior that are characteristic of confidence problems include being pessimistic and reacting to one's emotions without considering their source. Doing so can lead your boyfriend to seeing the world through the lens of his prevailing emotion, such as depression. It's possible that you can become accustomed to your boyfriend's confidence problems, to the point where you adopt them as your own. Be aware of your moods and behaviors and identify them as accurate or inaccurate.

Encourage your boyfriend to seek professional help to discuss his confidence problems. Approach the subject by prefacing your suggestion with assurance of your feelings for him, along with statements such as "I'm concerned about you." Your role, as his partner, isn't to "fix" his problems, although you do play a role and the problems innately affect you. Professionals in the field of counseling, social work or psychology have the experience and education that can help foster a therapeutic relationship between them and your boyfriend. Accompany your boyfriend to his appointments, if he and his chosen professional feel it will help his progress.

Express your feelings honestly about your boyfriend, to him. You may believe that your actions make plenty of statements about your feelings towards your boyfriend, but stating them makes them more concrete. Begin any statement of your feelings with "I feel," followed by how you feel. After that, add a specific example of the behavior that elicited your emotion, such as "I feel frustrated when you disagree with compliments that I give you." Always include an affirmation such as "I genuinely mean it when I give you a compliment." Remember that your intention is to give your boyfriend information about how you feel and what behaviors lead to that feeling.